The objectives of these studies are to develop a practical chiral reducing agent (or agents) for carbonyl and imino compounds which will be available in either enantiomeric form and which will give stereoselectivities above 90% for a wide spectrum of carbonyl and imino substrates. We have obtained substantial asymmetric reductions of carbonyl compounds using chiral hydride transfer reagents prepared by treating lithium aluminum hydride with three equivalents or less of a chiral aminocarbinol, designated LiAIHn (OR*) n-4. The complexes prepared from various derivatives of (plus)-(2S,3R)-4-dimethylamino-12-butanol such as the 3,5-dimethoxy, o-methoxy, p-phenyl and p-tert-butyl derivatives, have shown particular promise (asymmetric reductions of 65-95%). These reagents will be studied further in order to optimize the conditions of temperature, solvent, LiAIH4-carbinol-amine ratio, etc. In addition, several cyclic, more rigid analogs of these will be prepared. We will also be extending our studies on modified chiral homogeneous catalysts which are chiral both at carbon and phosphorus. X-ray crystallographic structure determinations will be attempted on suitable crystals both for the chiral LiAIH (OR*)3 and CH3PhP*-menthyl reagents.